2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 1-(2-(4-(2-Bromo-6-methoxynaphthalen-1-yloxy)phenoxy)ethyl)piperidine

HRID 445228Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 445228
[Br:1][C:2]1[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH3:13])[CH:8]=2)[C:3]=1[O:14][C:15]1[CH:29]=[CH:28][C:18]([O:19][CH2:20][CH2:21][N:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)=[CH:17][CH:16]=1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C(#N)C>[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH3:13])[CH:8]=2)[C:3]=1[O:14][C:15]1[CH:29]=[CH:28][C:18]([O:19][CH2:20][CH2:21][N:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)=[CH:17][CH:16]=1

Komponenten

4

Edukt 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 583385381-(2-(4-(2-Bromo-6-methoxy-3,4-dihydronaphthalen-1-yloxy)phenoxy)ethyl)piperidine

Produkt 1

HCID 583385631-(2-(4-(2-Bromo-6-methoxynaphthalen-1-yloxy)phenoxy)ethyl)piperidineAusbeute 27,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To a round bottom flask, add 1-(2-(4-(2-bromo-6-methoxy-3,4-dihydronaphthalen-1-yloxy)phenoxy)ethyl)piperidine (6.7 g, 6.6 mmol) and acetonitrile (50 mL). Stir the mixture at 25° C. for 5 min. Add 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) (3.2 g, 14.1 mmol) slowly to the reaction mixture. Heat the mixture to 80° C. and stir at the temperature for 14 hours. Cool the reaction mixture to room temperature and quench with ice-water. Extract the mixture with ethyl acetate three times and discard the aqueous phase. Dry the combined organic layers (MgSO4), filter, and concentrate to dryness. Purify by flash chromatography to give 1-(2-(4-(2-bromo-6-methoxynaphthalen-1-yloxy)phenoxy)ethyl)piperidine as a brown solid (817 mg). 1HNMR (d-DMSO, 300 MHZ): 7.68 (3H, m), 7.43 (1H, s), 7.15 (1H, m), 6.97 (2H, d), 6.72 (2H, d), 4.26 (2H, s), 3.85 (3H, s), 3.48 (4H, m), 2.96 (2H, m), 1.70 (6H, m).

Aufarbeitung

  1. temperatureHeat the mixture to 80° C.
  2. stirringstir at the temperature for 14 hours
  3. temperatureCool the reaction mixture to room temperature
  4. customquench with ice-water
  5. extractionExtract the mixture with ethyl acetate three times
  6. dry with materialDry the combined organic layers (MgSO4)
  7. filtrationfilter
  8. concentrationconcentrate to dryness
  9. customPurify by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-fed522ee1c354d17ac10ab97f995a778
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08476300B2

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